Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

Autor:	Robert McDonald, Brian A. Keay, Bronwen M. M. Wheatley, J. Matthew Hopkins, Evgueni Gorobets
Rok vydání:	2005
Předmět:	chemistry.chemical_compound Resolution (mass spectrometry) Chemistry Silica gel Heck reaction Yield (chemistry) Organic Chemistry Drug Discovery Diastereomer Organic chemistry Polyene Biochemistry Medicinal chemistry
Zdroj:	Tetrahedron Letters. 46:3843-3846
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2005.03.183
Popis:	The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of 1 (R = OtBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3′-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c33d8962ac44572b652eb4d3e4b23e94 https://doi.org/10.1016/j.tetlet.2005.03.183 Zobrazit plný text záznamu Full Text from ScienceDirect